This holiday season, Timberland makes it easy to show love to the people—your people—that matter most. From premium waterproof boots made to conquer slush-covered streets to everyday rotation-worthy staples, the heritage brand’s winter lineup is loaded with gift potential.
We picked 10 of Timberland’s coldest pieces that prove good style doesn’t stop when the temperature drops, whether you’re shopping for your outdoorsy friend, city commuter sister, or grandma who’s always cold.
Price: $180
Originating from the French “chore jacket,” the barn coat has transformed from practical wear for farmers and manual laborers in the early 1900s to a statement piece in 2025. Timberland’s take on the modern icon offers the ultimate crossover of function and form. The outer fabric is treated to be waterproof, making it a true rain or shine option.
Price: $120
The aesthetic of the Men’s Euro Hiker Boot is distinct from the original, 6-inch waterproof Timb, no question about it. The bold black exterior and relatively low cut gives the upper the look of a sneaker, while the outsole performs like a boot. The yin and yang effect breeds a hiking shoe that balances freedom of movement with sturdy support. It’s perfect for a person of the outdoors or a social urbanite.
Price: $150
This stylish Timberland jacket is a fit enhancer. The women’s version of the barn coat differs only slightly from the men’s in that it’s less boxy and slimmer fitting. The deep front pockets offer plenty of room for cold hands, gloves, and other belongings your girlfriend prefers not to lug around in a bag.
Price: $150
If you’re searching for a shoe that blends timeless style and cold-weather functionality, the Timberland Women’s Noreen Boat Shoe is a worthy pick. It features the qualities you’d expect from Timberland—premium, sturdy leather, a grippy lug outsole, hand-sewn craftsmanship—but in a silhouette that looks and feels refined enough for wearing at the office or going out with friends.
Price: $110
Made from 100% cotton, the chocolate brown Strafford Canvas Jacket fuses workwear DNA with street-ready polish. The corduroy collar, adjustable cuffs, and metal trims nod to retro utility, while the washed finish provides a rugged, lived-in aesthetic. It’s perfect for the person who lives to layer, be it over a hoodie or a flannel.
Price: $160
Built with high-grade waterproof leather, a rubber lug outsole and 200 grams of PrimaLoft® insulation (tech that is also used in pillows and comforters), the Waterproof Field Boot is equally trail tough as it is street-smart. The D-ring lacing system and padded collar provide stabilized, cushioned comfort, while the anti-fatigue footbed protects feet from the wear and tear of navigating winter slush, city sidewalks, and unfamiliar terrains.
Price: $55
Cooler temperatures outside typically translate to cooler temperatures inside. Timberland’s Northwood Brushed Back Hoodie will keep your loved ones warm and cozy on the most blistering of winter days. The laid back look is perfect for curling up on the couch to watch (or read) a winter favorite. The soft cotton-polyester blend may very well be the key to unlocking their comfy cold weather era.
Price: $200
This 14-inch tall silhouette has your tall friend covered. Literally. It takes an OG Timb and adds an extra shield for their legs. The waterproof leather and seam-sealed construction pair with an eco-conscious ReBOTL™ fabric lining that incorporates at least 50% recycled plastic, so they’ll feel good wearing the boot… and you’ll feel good gifting it to them.
Price: $70
Everyone needs a solid pair of blue jeans in their rotation. Timberland’s Sandown Slim Denim Pant for men has ‘new staple piece’ written all over it. Composed of 68% cotton, 31% TENCEL™ Lyocell (with REFIBRA® technology), and 1% elastane, the jeans offer a slim fit with just enough stretch to move freely. The pre-steamed denim helps resist shrinkage, while the classic five-pocket layout and subtle leather badge lend a timeless look.
Price: $140
When the weather gets rough in the city, one has to rise above it all in style. These Patent Leather Stone Street Platform Chukka can help the woman on your gift list do exactly that, with a 200 grams of PrimaLoft® insulation, a high-traction platform rubber outsole, steel support shank, and removable anti-fatigue footbeds that return energy to the foot. A chic high-shine patent leather upper helps tie the bow on the package, offering urbane sophistication with a kick.
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